This worked ON me once.
When I was 15, a guy a few houses down got me to start sucking him off. He was 17, str8 and had a long thin 8.5 with a big head on it. After a month or so of almost daily blowjobs, I guess he was wanting something different. He had been asking to fuck me, but I kept saying no. I was afraid it would hurt, and thought that was "too gay". lol. One day, he was laying back on the bed, with me between his legs sucking away. All the sudden he pulled me up beside him and turned me on my side with my back to him in a spooning position. He said he just wanted to rub his cock between my cheeks. He did this for a bit, every once in a while he"d rub his cockhead on my hole. He finally asked if he could just stick the head in to see what it felt like. I was turned on enough at this point that i said ok. He rubbed some vaseline on his cock, and then I felt his head on my hole. He gave a slow, steady push. It hurt like hell. I grinned and beared it. He let out a soft moan, and said the "head is in. It feels so great. Let me leave it here for a sec." After a few mins, he started a slow rocking motion. I was turned on and the pain was subsiding. Next thing I know, I feel his stomach against my ass and realize he's all the way inside me. He pulls almost all the way out and and the starts to slowly enter me again. After doing this a few more times, he starts to pick up the pace. At this point, he"s full on fucking me. We were both loving it. He didn't last long before he started cumming in my ass. It was the first of many times he fucked me and shot his load in my
ass.